Aromatic perfluoroalkane monomer

Abstract

An aromatic perfluoroalkane monomer is provided that can be used for the manufacture of a polymer membrane for a PEM-type fuel cell. The perfluoroalkane monomer has a structure corresponding to a formula (I): Z 1 —Ar 3 —C(O)—Ar 1 —(CF 2 ) n —Ar 2 —C(O)—Ar 4 —Z 2   (I) in which: n is in a range from 1 to 20; Ar 1 , Ar 2 , Ar 3 , Ar 4 which are identical or different, represent a substituted or unsubstituted phenylene group; and Z 1 and Z 2 , which are identical or different, represent an electrophilic or nucleophilic polymerizable functional group.

The invention claimed is: 
     
       1. An aromatic perfluoroalkane monomer corresponding to a formula (I):
   Z 1 —Ar 3 —C(═O)—Ar 1 —(CF 2 ) n —Ar 2 —C(═O)—Ar 4 —Z 2   (I)
 
 in which:
 n is in a range from 1 to 20, 
 Ar 1 , Ar 2 , Ar 3 , Ar 4  which are identical or different, represent an unsubstituted phenylene group or a phenylene group substituted with at least one substituent selected from the group consisting of —F, —Cl, —Br, —CN, —CF 3 , —NO 2 , —N(CH 3 ) 2 , —COOH, —COOM, —PO 3 H, —PO 3 M, —SO 3 H, —SO 3 M, hydroxyl, alkyl, cycloaklyl, perfluoroalkyl, sulphoalkyl, sulphoaryl, aryl, alkylcarbonyl, arylcarbonyl, alkoxyl and aryloxyl, where M is an alkali metal cation, and 
 Z 1  and Z 2 , which are identical or different, represent an electrophilic or nucleophilic polymerizable functional group. 
 
 
     
     
       2. The monomer according to  claim 1 , wherein n is in a range from 2 to 20. 
     
     
       3. The monomer according to  claim 1 , wherein n is in a range from 2 to 8. 
     
     
       4. The monomer according to  claim 1 , wherein Z 1  and Z 2 , which are identical or different, are chosen from the group consisting of halogen, hydroxyl, alkoxyl, thiol, carboxyl, carboxylate, amino, sulphonamido, acyl chloride, sulphonyl chloride, sulphonyl fluoride, isocyanate, and combinations thereof. 
     
     
       5. The monomer according to  claim 4 , wherein the monomer corresponds to a formula (I-2):
   F—Ar 3 —CO—Ar 1 —(CF 2 ) n —Ar 2 —CO—Ar 4 -F.  (I-2)
 
 
     
     
       6. The monomer according to  claim 4 , wherein the monomer corresponds to a formula (I-3):
   HO—Ar 3 —CO—Ar 1 —(CF 2 ) n —Ar 2 —CO—Ar 4 —OH.  (I-3)
 
 
     
     
       7. The monomer according to  claim 1 , wherein n is equal to 4. 
     
     
       8. The monomer according to  claim 2 , wherein n is equal to 4. 
     
     
       9. The monomer according to  claim 3 , wherein n is equal to 4. 
     
     
       10. The monomer according to  claim 4 , wherein n is equal to 4. 
     
     
       11. The monomer according to  claim 5 , wherein n is equal to 4. 
     
     
       12. The monomer according to  claim 6 , wherein n is equal to 4. 
     
     
       13. The monomer according to  claim 1 , wherein the monomer is a sulphonic monomer carrying a sulphonic (—SO 3 H) group or a sulphonate (—SO 3 M) group, in which M represents an alkali metal cation. 
     
     
       14. The monomer according to  claim 13 , wherein the sulphonic (—SO 3 H) group or the sulphonate (—SO 3 M) group is carried by a phenyl group or a phenylene group, or by a substituent thereof.